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High Hill Holiday Rentals

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Our top choices for High Hill holiday rentals

1. The Mercantile on the Katy Trail

The Mercantile on the Katy Trail
4.5 star property
Hermann
9.8 out of 10, Exceptional, (43 reviews)
"We loved this place- very unique! Clean and great communication from hosts."
United States
Kristine
The price is NZ$382
includes taxes & fees
1 Dec - 2 Dec
The Mercantile on the Katy Trail

2. The Cottage

The Cottage
2.0 star property
Hermann
10.0 out of 10, Exceptional, (1 review)
"Our host mentioned he does not receive messages from Expedia postings. So if you are not receiving check-in information, you might want to find another way to contact them. The property is lovely. The Treehouse was perfect for my granddaughter and me."
United States
Linda
The price is NZ$556
includes taxes & fees
8 Nov - 9 Nov
The Cottage

3. Gipfel Suite - Himmel Haus Bed & Breakfast

Gipfel Suite - Himmel Haus Bed & Breakfast
Hermann
10.0 out of 10, Exceptional, (144 reviews)
"The room was nice with a great shower. The breakfast was delicious."
United States
Peggy
The price is NZ$299
includes taxes & fees
10 Nov - 11 Nov
Gipfel Suite - Himmel Haus Bed & Breakfast

4. Bright Lakefront Studio Condo at Innsbrook

Bright Lakefront Studio Condo at Innsbrook
Wright City
9.8 out of 10, Exceptional, (74 reviews)
"everything was clean and really beautiful, we enjoyed the stay "
United States
Vanessa O.
The price is NZ$327
includes taxes & fees
8 Nov - 9 Nov
Bright Lakefront Studio Condo at Innsbrook

5. Zinfandel Room - Old Vine

Zinfandel Room - Old Vine
Hermann
10.0 out of 10, Exceptional, (33 reviews)
"Breakfast was amazing!"
United States
Amanda Q.
The price is NZ$318
includes taxes & fees
9 Nov - 10 Nov
Zinfandel Room - Old Vine

6. Secluded 2 bedroom home close to Hermann

Secluded 2 bedroom home close to Hermann
New Florence
9.8 out of 10, Exceptional, (52 reviews)
"Very nice place "
United States
Yaqui S.
The price is NZ$425
includes taxes & fees
19 Nov - 20 Nov
Secluded 2 bedroom home close to Hermann

7. Wine Alley East Suite

Wine Alley East Suite
Hermann
9.2 out of 10, Wonderful, (91 reviews)
"Host was great. Easy checkin and checkout. Great location to ride trolley to wineries and then walk Hermann at night."
United States
Sandy H.
The price is NZ$365
includes taxes & fees
8 Nov - 9 Nov
Wine Alley East Suite

8. Charming 2-bedroom house in fabulous downtown Hermann

Charming 2-bedroom house in fabulous downtown Hermann
Hermann
9.8 out of 10, Exceptional, (17 reviews)
"Cute older home, very clean, nice for a quick overnight stay."
United States
Sandy S.
The price is NZ$422
includes taxes & fees
1 Dec - 2 Dec
Charming 2-bedroom house in fabulous downtown Hermann

9. McKittrick Suite - Loft Stay on Katy Trail in Historic Mercantile, 4 min Hermann

McKittrick Suite - Loft Stay on Katy Trail in Historic Mercantile, 4 min Hermann
McKittrick
10.0 out of 10, Exceptional, (2 reviews)
"Loved this placed, would definitely come back!"
United States
Cody W.
McKittrick Suite - Loft Stay on Katy Trail in Historic Mercantile, 4 min Hermann

10. Depot Suite - Ground-Floor Historic Loft on Katy Trail, 4 Mins to Hermann Wineries

Depot Suite - Ground-Floor Historic Loft on Katy Trail, 4 Mins to Hermann Wineries
Hermann
10.0 out of 10, Exceptional, (4 reviews)
"So pretty and perfect for our weekend."
United States
Katherine B.
The price is NZ$463
includes taxes & fees
8 Dec - 9 Dec
Depot Suite - Ground-Floor Historic Loft on Katy Trail, 4 Mins to Hermann Wineries

11. Vaudeville Suite, Romantic King Stay Just 4 Min from Hermann Wineries

Vaudeville Suite, Romantic King Stay Just 4 Min from Hermann Wineries
Hermann
The price is NZ$463
includes taxes & fees
8 Dec - 9 Dec
Vaudeville Suite, Romantic King Stay Just 4 Min from Hermann Wineries

12. Cozy Wooded Retreat 3 minutes from Hermann ~ Nature`s Nook

Cozy Wooded Retreat 3 minutes from Hermann ~ Nature`s Nook
Hermann
10.0 out of 10, Exceptional, (8 reviews)
"This place is AMAZING. It is beautiful and such a peaceful get away. Just a quick 5 minute drive to town, but you feel like you’re miles away. The property was beautiful and the space was peaceful and secluded. Highly recommend. "
United States
Patti
Cozy Wooded Retreat 3 minutes from Hermann ~ Nature`s Nook

13. Ash Creek Suite - In Downtown Historic Hermann

Ash Creek Suite - In Downtown Historic Hermann
Hermann
9.4 out of 10, Exceptional, (56 reviews)
"Great place! Great location! And clean!"
United States
Cheryl E.
The price is NZ$443
includes taxes & fees
8 Dec - 9 Dec
Ash Creek Suite - In Downtown Historic Hermann

14. Wine Alley West Suite

Wine Alley West Suite
Hermann
9.0 out of 10, Wonderful, (61 reviews)
"Good location with an easy walk to downtown shops. Communication and flexibility on checking in was very good and much appreciated. Apartment worked out great for my trip thru Herman."
United States
Clyde O.
The price is NZ$369
includes taxes & fees
19 Nov - 20 Nov
Wine Alley West Suite

15. 3-bedroom family friendly home on 4 acres near Hermann with WiFi, AC, deck

3-bedroom family friendly home on 4 acres near Hermann with WiFi, AC, deck
Hermann
9.8 out of 10, Exceptional, (19 reviews)
"Host was very accommodating, property perfect, I can't say enough good things about our stay."
United States
Susan R.
The price is NZ$719
includes taxes & fees
19 Nov - 20 Nov
3-bedroom family friendly home on 4 acres near Hermann with WiFi, AC, deck

16. Germantown Inn & Lounge RM 5

Germantown Inn & Lounge RM 5
Hermann
10.0 out of 10, Exceptional, (2 reviews)
"This was very quaint, comfortable, and in the middle of the action - walking distance to everything. I would definitely book again."
United States
Victoria
The price is NZ$382
includes taxes & fees
6 Dec - 7 Dec
Germantown Inn & Lounge RM 5

17. Back Door Guest Suite, Zia My Retreat

Back Door Guest Suite, Zia My Retreat
New Haven
10.0 out of 10, Exceptional, (8 reviews)
"Very comfortable, spacious, great location for canoe trip. "
United States
Carolyn B.
The price is NZ$392
includes taxes & fees
8 Nov - 9 Nov
Back Door Guest Suite, Zia My Retreat

18. Hickory Lake House

Hickory Lake House
3.0 star property
Wright City
The price is NZ$786
includes taxes & fees
13 Nov - 14 Nov
Hickory Lake House

19. Cozy Riverview Cottage. 5 minute walk to downtown

Cozy Riverview Cottage. 5 minute walk to downtown
Hermann
10.0 out of 10, Exceptional, (66 reviews)
"The cottage was very charming and a great location to downtown Hermann!"
United States
Sheila L.
The price is NZ$458
includes taxes & fees
8 Nov - 9 Nov
Cozy Riverview Cottage. 5 minute walk to downtown

20. Papa's Cabin - 40 acres & 5 acre lake!

Papa's Cabin - 40 acres & 5 acre lake!
Middletown
10.0 out of 10, Exceptional, (4 reviews)
"Overall stay was amazing! The property was just like described and the hostess was easy to communicate with."
United States
Prisilla B.
The price is NZ$363
includes taxes & fees
21 Nov - 22 Nov
Papa's Cabin - 40 acres & 5 acre lake!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top High Hill Hotel Reviews

Find out more about High Hill

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our High Hill holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up High Hill. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in High Hill. Seeing all the best attractions is bound to make you fall in love with High Hill. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in High Hill short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there holiday rentals in High Hill?

Yes, there are holiday rentals close to the most popular sights in High Hill, or you can select a more secluded option if you're looking for a relaxing stay. High Hill is known for its coffee shops and restaurants.

What are some of the best holiday rentals that High Hill has to offer?

Cozy Riverview Cottage. 5 minute walk to downtown: This holiday home rental outside of High Hill is equipped with a patio, air conditioning and a Smart TV to help you feel comfortable during your stay. Kitchen amenities include a dishwasher, a fridge and a stovetop.

What can I see and do in High Hill?

While you're exploring the area, Graham Cave State Park and Katy Trail - McKittrick Trailhead are a couple of picturesque spots to get outside and enjoy nature. In the wider area, you’ll find Endless Summer Winery and OakGlenn Vineyards and Winery.

What are holiday rentals like in High Hill?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in High Hill. Holiday rentals feature extras like WiFi and washers and dryers so you'll feel just like you're at home. If you're concerned about a clean environment, a holiday rental can offer a sense of safety away from public hotel lifts and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is an attractive choice for a family trip.